EP0011295A1 - Colorants monoazoiques jaunes de la série des 2-hydroxydibenzofurannes, leur préparation et leur utilisation à la teinture et l'impression de fibres synthétiques hydrophobes - Google Patents
Colorants monoazoiques jaunes de la série des 2-hydroxydibenzofurannes, leur préparation et leur utilisation à la teinture et l'impression de fibres synthétiques hydrophobes Download PDFInfo
- Publication number
- EP0011295A1 EP0011295A1 EP79104521A EP79104521A EP0011295A1 EP 0011295 A1 EP0011295 A1 EP 0011295A1 EP 79104521 A EP79104521 A EP 79104521A EP 79104521 A EP79104521 A EP 79104521A EP 0011295 A1 EP0011295 A1 EP 0011295A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- group
- amino
- dyes
- formula
- dyeing
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
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- 239000000975 dye Substances 0.000 title claims abstract description 24
- 238000004043 dyeing Methods 0.000 title claims abstract description 14
- 238000007639 printing Methods 0.000 title claims abstract description 9
- 230000002209 hydrophobic effect Effects 0.000 title claims abstract description 4
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 title claims abstract description 4
- HGIDRHWWNZRUEP-UHFFFAOYSA-N 2-hydroxydibenzofuran Chemical class C1=CC=C2C3=CC(O)=CC=C3OC2=C1 HGIDRHWWNZRUEP-UHFFFAOYSA-N 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 229920000728 polyester Polymers 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims abstract description 5
- -1 sulphonamido group Chemical group 0.000 claims abstract description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000004429 atom Chemical group 0.000 claims abstract description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 3
- 239000000460 chlorine Substances 0.000 claims abstract description 3
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- 229920000742 Cotton Polymers 0.000 claims description 5
- BQQFSUKXGGGGLV-UHFFFAOYSA-N 1-phenylpyrazol-3-amine Chemical class N1=C(N)C=CN1C1=CC=CC=C1 BQQFSUKXGGGGLV-UHFFFAOYSA-N 0.000 claims description 4
- 230000001590 oxidative effect Effects 0.000 claims description 4
- KEQTWHPMSVAFDA-UHFFFAOYSA-N 2,3-dihydro-1h-pyrazole Chemical compound C1NNC=C1 KEQTWHPMSVAFDA-UHFFFAOYSA-N 0.000 claims description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 3
- 238000006193 diazotization reaction Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- 229920002994 synthetic fiber Polymers 0.000 abstract description 2
- 239000000835 fiber Substances 0.000 abstract 1
- 239000012209 synthetic fiber Substances 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 10
- BPLNQWRKOHDDDN-UHFFFAOYSA-N 2-phenyl-1,3-dihydropyrazol-5-amine Chemical class N1C(N)=CCN1C1=CC=CC=C1 BPLNQWRKOHDDDN-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- YDUASLIZTNJBLQ-UHFFFAOYSA-N 1-(3-chlorophenyl)pyrazol-3-amine Chemical compound N1=C(N)C=CN1C1=CC=CC(Cl)=C1 YDUASLIZTNJBLQ-UHFFFAOYSA-N 0.000 description 2
- NZNXVABRGBFJED-UHFFFAOYSA-N 3-diazopyrazole Chemical class [N-]=[N+]=C1C=CN=N1 NZNXVABRGBFJED-UHFFFAOYSA-N 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- VQTGUFBGYOIUFS-UHFFFAOYSA-N nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- 238000007669 thermal treatment Methods 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- OQDMCDIRPZVTFZ-UHFFFAOYSA-N 1,3-dihydropyrazol-2-amine Chemical class NN1CC=CN1 OQDMCDIRPZVTFZ-UHFFFAOYSA-N 0.000 description 1
- GFDOAHVWCUSZCS-UHFFFAOYSA-N 1,5-diphenylpyrazol-3-amine Chemical compound C=1C=CC=CC=1N1N=C(N)C=C1C1=CC=CC=C1 GFDOAHVWCUSZCS-UHFFFAOYSA-N 0.000 description 1
- YWHGDEVUWSGERT-UHFFFAOYSA-N 1-(2,4,5-trichlorophenyl)pyrazol-3-amine Chemical compound N1=C(N)C=CN1C1=CC(Cl)=C(Cl)C=C1Cl YWHGDEVUWSGERT-UHFFFAOYSA-N 0.000 description 1
- JMZWCUDIHPEHTE-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)pyrazol-3-amine Chemical compound N1=C(N)C=CN1C1=CC=C(Cl)C=C1Cl JMZWCUDIHPEHTE-UHFFFAOYSA-N 0.000 description 1
- YKEJZQWYPCXLFH-UHFFFAOYSA-N 1-(2,5-dichlorophenyl)pyrazol-3-amine Chemical compound N1=C(N)C=CN1C1=CC(Cl)=CC=C1Cl YKEJZQWYPCXLFH-UHFFFAOYSA-N 0.000 description 1
- PEJLBNVUSCTMEX-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)pyrazol-3-amine Chemical compound N1=C(N)C=CN1C1=CC=C(Cl)C(Cl)=C1 PEJLBNVUSCTMEX-UHFFFAOYSA-N 0.000 description 1
- BZEBCGYFUBGJOT-UHFFFAOYSA-N 1-(3-chlorophenyl)-5-phenylpyrazol-3-amine Chemical compound C=1C=CC(Cl)=CC=1N1N=C(N)C=C1C1=CC=CC=C1 BZEBCGYFUBGJOT-UHFFFAOYSA-N 0.000 description 1
- OYEGYZKYEVYAFG-UHFFFAOYSA-N 1-(3-nitrophenyl)pyrazol-3-amine Chemical compound N1=C(N)C=CN1C1=CC=CC([N+]([O-])=O)=C1 OYEGYZKYEVYAFG-UHFFFAOYSA-N 0.000 description 1
- GZDIUHKAZLMQFJ-UHFFFAOYSA-N 1-(4-bromophenyl)pyrazol-3-amine Chemical compound N1=C(N)C=CN1C1=CC=C(Br)C=C1 GZDIUHKAZLMQFJ-UHFFFAOYSA-N 0.000 description 1
- SHCVEWFQFUKSDP-UHFFFAOYSA-N 1-(4-chlorophenyl)pyrazol-3-amine Chemical compound N1=C(N)C=CN1C1=CC=C(Cl)C=C1 SHCVEWFQFUKSDP-UHFFFAOYSA-N 0.000 description 1
- PUYOZGLXKYWMBT-UHFFFAOYSA-N 1-(4-methoxyphenyl)pyrazol-3-amine Chemical compound C1=CC(OC)=CC=C1N1N=C(N)C=C1 PUYOZGLXKYWMBT-UHFFFAOYSA-N 0.000 description 1
- UGUPUADULADGJC-UHFFFAOYSA-N 1-(4-nitrophenyl)pyrazol-3-amine Chemical compound N1=C(N)C=CN1C1=CC=C([N+]([O-])=O)C=C1 UGUPUADULADGJC-UHFFFAOYSA-N 0.000 description 1
- LCLWEOIMXMEDKX-UHFFFAOYSA-N 1-[3-(trifluoromethyl)phenyl]pyrazol-3-amine Chemical compound N1=C(N)C=CN1C1=CC=CC(C(F)(F)F)=C1 LCLWEOIMXMEDKX-UHFFFAOYSA-N 0.000 description 1
- XRKJFSFMYUQOSD-UHFFFAOYSA-N 2-(2-chlorophenyl)benzene-1,4-diol Chemical compound OC1=CC=C(O)C(C=2C(=CC=CC=2)Cl)=C1 XRKJFSFMYUQOSD-UHFFFAOYSA-N 0.000 description 1
- PXKUDMRTHTXSAK-UHFFFAOYSA-N 3-(3-aminopyrazol-1-yl)benzonitrile Chemical compound N1=C(N)C=CN1C1=CC=CC(C#N)=C1 PXKUDMRTHTXSAK-UHFFFAOYSA-N 0.000 description 1
- NXLPRPBPDJSFNI-UHFFFAOYSA-N 3-methyl-2-phenyl-1,3-dihydropyrazol-5-amine Chemical compound CC1C=C(N)NN1C1=CC=CC=C1 NXLPRPBPDJSFNI-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- BZNNASVPSAVYSJ-UHFFFAOYSA-N 4-(5-amino-1,3-dihydropyrazol-2-yl)benzonitrile Chemical compound C(#N)C1=CC=C(C=C1)N1NC(=CC1)N BZNNASVPSAVYSJ-UHFFFAOYSA-N 0.000 description 1
- VKJMGEGMWDCHPA-UHFFFAOYSA-N 4-methyl-1-phenylpyrazol-3-amine Chemical compound N1=C(N)C(C)=CN1C1=CC=CC=C1 VKJMGEGMWDCHPA-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- FWPZFPRKAAHGBB-UHFFFAOYSA-N BrC1=C(C=C(C=C1)Br)N1NC(=CC1)N Chemical compound BrC1=C(C=C(C=C1)Br)N1NC(=CC1)N FWPZFPRKAAHGBB-UHFFFAOYSA-N 0.000 description 1
- AISOMESGJQTEOZ-UHFFFAOYSA-N BrC=1C=C(C=C(C1Br)Br)N1NC(=CC1)N Chemical compound BrC=1C=C(C=C(C1Br)Br)N1NC(=CC1)N AISOMESGJQTEOZ-UHFFFAOYSA-N 0.000 description 1
- SKBQCHVBIKRICB-UHFFFAOYSA-N COC=1C=C(C=C(C1)OC)N1NC(=CC1)N Chemical compound COC=1C=C(C=C(C1)OC)N1NC(=CC1)N SKBQCHVBIKRICB-UHFFFAOYSA-N 0.000 description 1
- AOOHGJFYDYACJV-UHFFFAOYSA-N ClC1=C(C(=CC=C1)Cl)N1NC(=CC1)N Chemical compound ClC1=C(C(=CC=C1)Cl)N1NC(=CC1)N AOOHGJFYDYACJV-UHFFFAOYSA-N 0.000 description 1
- HOZQVDDYWLSDKL-UHFFFAOYSA-N NC=1NN(C(C1)C1=CC=CC=C1)C1=CC=C(C=C1)Cl Chemical compound NC=1NN(C(C1)C1=CC=CC=C1)C1=CC=C(C=C1)Cl HOZQVDDYWLSDKL-UHFFFAOYSA-N 0.000 description 1
- ILVZHTLYLYNITL-UHFFFAOYSA-N NC=1NN(CC1)C1=CC(=C(C=C1)Br)Br Chemical compound NC=1NN(CC1)C1=CC(=C(C=C1)Br)Br ILVZHTLYLYNITL-UHFFFAOYSA-N 0.000 description 1
- DHZJDUSYLOYLLZ-UHFFFAOYSA-N NC=1NN(CC1)C1=CC(=CC=C1)Br Chemical compound NC=1NN(CC1)C1=CC(=CC=C1)Br DHZJDUSYLOYLLZ-UHFFFAOYSA-N 0.000 description 1
- PXFGMIDPFHNCCG-UHFFFAOYSA-N NC=1NN(CC1)C1=CC=C(C=C1)OCC Chemical compound NC=1NN(CC1)C1=CC=C(C=C1)OCC PXFGMIDPFHNCCG-UHFFFAOYSA-N 0.000 description 1
- 229910004878 Na2S2O4 Inorganic materials 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- YWWCUROHCLSOQG-UHFFFAOYSA-N [N+](=O)([O-])C1=C(C=CC(=C1)[N+](=O)[O-])N1NC(=CC1)N Chemical compound [N+](=O)([O-])C1=C(C=CC(=C1)[N+](=O)[O-])N1NC(=CC1)N YWWCUROHCLSOQG-UHFFFAOYSA-N 0.000 description 1
- 229910052656 albite Inorganic materials 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 239000001166 ammonium sulphate Substances 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3678—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only oxygen as heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
- C09B29/0029—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom
- C09B29/0037—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom containing a five-membered heterocyclic ring with two nitrogen atoms
Definitions
- This invention relates to a new class of water-insoluble yellow monoazo dyes.
- the present invention relates furthermore to the preparation of the dyes of formula (I) and the use of same.
- the dyes object of this invention are particularly suitable for dyeing and printing hydrophobic synthetic fibres, in particular polyester fibres, with yellow shades.
- the dyes of the present invention exhibit a high stability to light, to wet treatments and to heat treatments.
- the dyes of the present invention have furthermore exhibited an excellent behaviour in the dyeing and printing of polyester-cotton blended fibres, according to known processes used at present, as they have all the main characteristics required for this application, i.e.:
- the dyes forming the object of this invention are obtained by diazotizing, according to substantially conventional methods, the 1-phenyl-3-amino pyrazols of formula (II) as defined hereinbefore, and by successively coupling, in an acid to basic medium, the diazopyrazols obtained on 2-hydroxy-dibenzofuran of formula (III).
- the dyes of the present invention can be also prepared by oxidative diazotization of 1-phenyl-3-amino pyrazolins having formula (IV): wherein R , R , X and n have the meanings indicated herein above; in this manner it is possible to obtain the corresponding diazopyrazols, which are then coupled on 2 -hydroxy--dibenzofuran of formula (III), as explained hereinbefore.
- the abovesaid oxidative diazotation of the pyrazolins of formula (IV) is efficaciously conducted, for example, according to the method forming the object of Italian patent application No. 23725 A/78, according to which the amino-pyrazolins of formula (IV) are treated with nitrous acid in a ratio of from 2:1 to 5:1 in respect of amino-py razolins (IV), in an organic acid medium (acetic or propionic acid) or in an inorganic acid medium (hydrochloric acid, sulphuric acid, etc.) at a temperature in the range of from -10°C to +20°C.
- the nitrous acid in its turn, is prepared from alkaline or alkyl nitrites, or from nitrosyl-sulphuric acid.
- 1-phenyl-3-amino pyrazolins (IV) can be prepared by conventional methods.
- 1-phenyl-3-amino pyrazols (II) can be obtained, in their turn, by oxidizing the corresponding pyrazolins (IV), for example with chloranil in xylene (C. Alberti. Il Farmaco - Ed. Sc. vol. XIX, issue 7, page 638), or by flowing of air through an inert solvent (alcohols, acetic acid, aceto nitrile) in the presence of copper salts (CuCl, CuCl , acetate) at about 20°C-40°C, as described in Belgian patent application No. 855,944 filed by the Applicant.
- 2-hydroxy-dibenzofuran (III) can be prepared for example from 2-(2'-chlorophenyl)-hydroquinone by heating with NaOH or KOH (US patent No. 2,172,572).
- the dye obtained after drying was a yellow powder having the following centesimal composition: .
- the resulting diazo solution was let into 200 g of ice and 100 ml of water, and the nitrous acid in excess was removed by means ⁇ f sulphamic acid.
- the diazo solution was dropped, at a temperature of from 5° to 10°C, into a solution consisting of 1.84 g (0.01 moles) of 2-hydroxy-dibenzofuran, 100 ml of 36° Be sodium hydrate and 600 ml of water.
- the yellow dyeing so obtained possessed a high intensity and excellent stabilities to sunlight, to moisture and to thermal treatments.
- the dried fabric retaining however ah amount of solvent useful to fix the dye, was heat set in warm air at 200°C for 1-2 minutes.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT29817/78A IT1101703B (it) | 1978-11-15 | 1978-11-15 | Itcoloranti monoazoici gialli |
IT2981778 | 1978-11-15 |
Publications (1)
Publication Number | Publication Date |
---|---|
EP0011295A1 true EP0011295A1 (fr) | 1980-05-28 |
Family
ID=11228496
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP79104521A Withdrawn EP0011295A1 (fr) | 1978-11-15 | 1979-11-15 | Colorants monoazoiques jaunes de la série des 2-hydroxydibenzofurannes, leur préparation et leur utilisation à la teinture et l'impression de fibres synthétiques hydrophobes |
Country Status (2)
Country | Link |
---|---|
EP (1) | EP0011295A1 (fr) |
IT (1) | IT1101703B (fr) |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1424732A (fr) * | 1964-02-14 | 1966-01-14 | Hoechst Ag | Procédé de teinture et impression, notamment de polypropylène contenant du nickel |
DE1240601B (de) * | 1962-02-28 | 1967-05-18 | Hoechst Ag | Verfahren zur Herstellung von metallhaltigen, wasserunloeslichen Azofarbstoffen |
GB1531697A (en) * | 1976-06-25 | 1978-11-08 | Montedison Spa | Pyrazole-azo-pyridone dyes |
-
1978
- 1978-11-15 IT IT29817/78A patent/IT1101703B/it active
-
1979
- 1979-11-15 EP EP79104521A patent/EP0011295A1/fr not_active Withdrawn
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1240601B (de) * | 1962-02-28 | 1967-05-18 | Hoechst Ag | Verfahren zur Herstellung von metallhaltigen, wasserunloeslichen Azofarbstoffen |
FR1424732A (fr) * | 1964-02-14 | 1966-01-14 | Hoechst Ag | Procédé de teinture et impression, notamment de polypropylène contenant du nickel |
GB1531697A (en) * | 1976-06-25 | 1978-11-08 | Montedison Spa | Pyrazole-azo-pyridone dyes |
Also Published As
Publication number | Publication date |
---|---|
IT1101703B (it) | 1985-10-07 |
IT7829817A0 (it) | 1978-11-15 |
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